Triphenylamine-benzothiophene organic small-molecule hole transporting material and application thereof

A hole transport material, benzothiophene technology, applied in the field of solar cell materials, can solve problems such as poor stability, and achieve the effect of improving stability, outstanding effect, and broadening the molecular conjugated system

Inactive Publication Date: 2016-07-13
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the shortcomings of the poor stability of perovskite solar cells in the prior art, the purpose of the present invention is to provide a heterocyclic ring containing a conjugated system and a triphenylamine structural unit with an alkyl side chain, which has good hydrophobicity and organic Solvent-soluble triphenylamine-benzothiophene organic small molecule hole transport material, which can be used in perovskite solar cells and can improve battery stability

Method used

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  • Triphenylamine-benzothiophene organic small-molecule hole transporting material and application thereof
  • Triphenylamine-benzothiophene organic small-molecule hole transporting material and application thereof
  • Triphenylamine-benzothiophene organic small-molecule hole transporting material and application thereof

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Experimental program
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Effect test

Embodiment 1

[0046] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport materials with structural units of formula II.

[0047] A kind of triphenylamine-benzothiophene organic small molecule hole transport material with chemical structure II, its synthesis route is as follows:

[0048]

[0049] Synthesis of intermediate (2):

[0050] 2.2 g of compound 1, 1.4 g of zinc powder and 30 mL of water were added to a 100 mL three-necked flask, and then 6 g of NaOH was added, and the mixture was heated to reflux for 1 hour. Then, add 5.0g of bromo-n-hexane and the equivalent of the catalyst tetrabutylammonium bromide (Bu 4 NBr), the reaction was heated to reflux for 6h. The mixture was poured into ice water, extracted twice with 200 mL of THF, the organic phase was dried with anhydrous magnesium sulfate, and after the solvent was removed by rotary evaporation, the initial product was recrystallized with absolute ethanol to obtain white crystals with a yield of 80%.

[0051] NM...

Embodiment 2

[0074] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport materials of chemical structure III.

[0075] A chemical structure formula triphenylamine-benzothiophene organic small molecule hole transport material, and its synthesis route is as follows:

[0076]

[0077] Synthesis of intermediate (6):

[0078] Add 10g 4-iodophenol, 8.9g bromoisooctane, 19g potassium carbonate and 150mL DMF into a 250mL three-necked reaction flask, under nitrogen protection, reflux and stir for 12h at 120°C. Then the mixture was poured into 1M NaOH aqueous solution, extracted with dichloromethane, and the organic liquids were combined, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated by rotary evaporation, and the crude product was separated and purified by column chromatography to obtain a colorless liquid with a yield of 53%.

[0079] NMR characterization data of intermediate (6):

[0080] 1 HNMR(CDCl 3 ,500MHz),δ(ppm):7.57(d,J=8.5,2H),6.70(d,...

Embodiment 3

[0102] Synthesis of triphenylamine-benzothiophene organic small molecule hole transport materials of chemical structure IV.

[0103] A kind of triphenylamine-benzothiophene organic small molecule hole transport material of chemical structure IV, its synthesis route is as follows:

[0104]

[0105] Synthesis of intermediate (10):

[0106] Dissolve 5.7g monomer M3 and 2.2g compound 9 in 45mL toluene, then add 2MK 2 CO 3 (12mL) aqueous solution, nitrogen protection, add 0.1mg catalyst Pd(PPh 3 ) 4 , Stir vigorously for 24h at 110℃. The mixture was cooled to room temperature, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and separated and purified by column chromatography to obtain Intermediate 10 with a yield of 64%.

[0107] NMR characterization data of intermediate (10):

[0108] 1 HNMR(400MHz, CDCl 3 ,ppm):δ8.75(s2H), 7.80(d,1H), 7.74(d,1H), 7.69-7.65(m,3H), 7.32(d,2H), 7.25(d,4H), 7.01( ...

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Abstract

The invention discloses a triphenylamine-benzothiophene organic small-molecule hole transporting material and an application thereof.The material has a specific heterocycle conjugated system and triphenylamine structural units with alkyl chains, and the solubleness and the hydrophobicity are good in an organic solvent; as the hole mobility can be effectively improved through a large two-dimensional conjugate plane structure, the material is applied to a perovskite solar cell, the stability of a device can be improved, the current density and the high photoelectric conversion rate are increased, and the material has the broad application prospects.

Description

Technical field [0001] The invention relates to an organic small molecule hole transport functional material and its application, in particular to a triphenylamine-benzothiophene organic small molecule hole transport material and its application as an energy conversion material, belonging to the technical field of solar cell materials . Background technique [0002] As we all know, as the economy continues to develop, the ecological environment continues to deteriorate, and energy is increasingly depleted. Finding sustainable green new energy to change the current severe energy situation has become the most important goal of scientists from all over the world. Among the many existing new energy sources, solar energy has received widespread attention because of its abundant reserves on the earth, wide irradiation range, and clean and pollution-free advantages. The solar cells designed based on the principle of photovoltaic effect are the most potential and fastest-growing new ene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D519/00H01L51/42H01L51/46
CPCC07D495/04C07D519/00H10K85/6576H10K30/00Y02E10/549
Inventor 潘春跃王海珍喻桂朋侯宇轩周贤勇
Owner CENT SOUTH UNIV
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